Franciscan convents have historically played a decisive role in the social and spatial construction of European cities, shaping the urban fabric through their scale, configuration, and strategic location along edges, infrastructures, and waterways. However, the suppression of religious orders during the Napoleonic era initiated a long-term transformation, converting many of these complexes into military barracks and marking a progressive detachment from their original liturgical and communal functions. Today, many of these former conventual complexes remain abandoned. This paper argues that their transformations cannot be understood solely as functional or programmatic changes, but entail a deeper negotiation with loss: the disappearance of religious and meditative practices, symbolic systems, and forms of collective inhabitation. With reference to the Italian context and strategies promoted by the State Property Agency, the paper examines how reuse processes engage—often implicitly—with the persistence of a sacred dimension. These complexes, shaped by monastic, military, and civic stratifications, are interpreted not as neutral containers, but as atmospherically and culturally dense environments. Through a comparative analysis of two case studies in Flanders developed through the Open Call mechanism—the Abbey of Saint Godelieve in Bruges and the Beguinage of Hasselt—the research investigates how design strategies address both material and immaterial dimensions of transformation, highlighting tensions between conservation and reinterpretation. Finally, the paper applies this critical re-reading to the Convent of Santa Maria della Ripa in Forlì, proposing an approach that integrates architectural, experiential, and symbolic parameters. From this perspective, adaptive reuse is not a neutralization of religious space, but an ongoing process negotiating between presence and absence, memory and transformation, and individual and collective spatial dimensions.